Triethylamine → HCID 11825571, 화합물

HRID 1984767노트

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HRID 1984767 반응식
[C:1]([O:5][C:6](=[O:19])[C:7]([NH:11]C(OC(C)(C)C)=O)([CH3:10])[CH2:8][OH:9])([CH3:4])([CH3:3])[CH3:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(N(CC)CC)C.[CH3:39][O:40][C:41]1[CH:46]=[CH:45][C:44]([CH:47]([C:49]2[CH:54]=[CH:53][C:52]([O:55][CH3:56])=[CH:51][CH:50]=2)Cl)=[CH:43][CH:42]=1>C(OCC)C.CCO>[C:1]([O:5][C:6](=[O:19])[C:7]([NH:11][CH:47]([C:49]1[CH:54]=[CH:53][C:52]([O:55][CH3:56])=[CH:51][CH:50]=1)[C:44]1[CH:45]=[CH:46][C:41]([O:40][CH3:39])=[CH:42][CH:43]=1)([CH3:10])[CH2:8][OH:9])([CH3:4])([CH3:2])[CH3:3]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 521998p-Toluenesulfonic acid monohydrateHCID 10706646bis(4-methoxyphenyl)chloromethaneHCID 111193112-[N-(tert-butoxycarbonyl)amino]-3-hydroxy-2-methylpropanoic acid tert-butyl ester

생성물 1

HCID 11825571HCID 11825571, 화합물

시약·촉매·용매 2

HCID 702Ethanol용매HCID 3283Diethyl Ether용매

실험 절차

To a solution of the alcohol 9 (100 mg, 0.36 mmol) in 2 mL of diethyl ether was added 1 eq of p-toluenesulfonic acid monohydrate (69 mg) dissolved in 6 mL of EtOH. The reaction mixture was concentrated under reduced pressure at 40° C., and the residue was dissolved in 6 mL of EtOH and concentrated again. This process was repeated 4 times, at which time no starting material was present on TLC analysis. The resulting white solid was suspended in 3 mL of CH2Cl2, and treated with 4.5 eq of triethylamine (0.23 mL) followed by 1 eq of bis(4-methoxyphenyl)chloromethane (95 mg). The reaction mixture was stirred for 1 hour at room temperature. The solution was then partitioned between 10 mL of EtOAc and 10 mL of H2O. The aqueous layer was extracted with 10 mL of EtOAc followed by the usual work up of the combined organic layers. Purification by silica gel column chromatography (20% EtOAc in hexane) provided the amino ester 12a as a colorless oil (107 mg, 73% from 9): 1H NMR (CDCl3) δ 1.17 (3H, s), 1.46 (9H, s), 3.35 (1H, d, J=11.2), 3.44 (1H, d, J=11.2), 3.76 (3H, s), 3.77 (3H, s), 4.82 (1H, s), 6.80-6.84 (4H, m), 7.27-7.31 (4H, m). Anal. (C23H31NO5)C,H,N.

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure at 40° C.
  2. dissolutionthe residue was dissolved in 6 mL of EtOH
  3. concentrationconcentrated again
  4. customThe solution was then partitioned between 10 mL of EtOAc and 10 mL of H2O
  5. extractionThe aqueous layer was extracted with 10 mL of EtOAc
  6. customPurification by silica gel column chromatography (20% EtOAc in hexane)

출처 및 근거

ORD 기록
ord-0da8435ab3a94467b6482a5b28f5376c
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07544715B2

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